Potassium Carbonate → HCID 86651270, compound

Temperature

45 °C

To a mixture of 2,6-dichloro-4-hydroxybenzaldehyde (1.00 g, 5.24 mmol) and K2CO3 (1.45 g, 10.5 mmol) in THF (25 mL) under N2 was added dropwise1-bromomethyl-4-methoxybenzene (1.10 mL, 7.85 mmol). The reaction was heated at 65° C. for 3 h, at 45° C. overnight then at 65° C. for 3 hr. The reaction was allowed to cool to ambient temperature then was filtered and the filtrate concentrated under reduced pressure. The concentrate was diluted with EtOAc (150 mL) and extracted with water (30 mL). The organic phase was dried over Na2SO4 and evaporated. The residue was purified by silica gel chromatography using a gradient of 5-15% EtOAc/heptane as eluent to afford 2,6-dichloro-4-(4-methoxybenzyloxy)-benzaldehyde as a white solid. MS (m/z) 311.0 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 10.28 (s, 1H), 7.40 (d, J=8.59 Hz, 2H), 7.29 (s, 2H), 6.97 (d, J=8.72 Hz, 2H), 5.19 (s, 2H), 3.76 (s, 3H).

1. temperatureto cool to ambient temperature
2. filtrationthen was filtered
3. concentrationthe filtrate concentrated under reduced pressure
4. additionThe concentrate was diluted with EtOAc (150 mL)
5. extractionextracted with water (30 mL)
6. dry with materialThe organic phase was dried over Na2SO4
7. customevaporated
8. customThe residue was purified by silica gel chromatography

ORD record

ord-23162b2601d44f9ba9c896a7000087c0

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2